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$79+ Cheap flights from Vermont to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
BTV — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap flight deals from Vermont to Chicago

Keep the following information in mind while searching for Vermont to Chicago flight deals. Data was last updated July 3, 2025.

Round-trip from

$210
(Delta)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

May

Average price

$338

Good round-trip deal

$367 or less

Good one-way deal

$258 or less
From Vermont to Chicago (CHI)
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One-way flight from Vermont to Chicago (CHI)
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Vermont to Chicago (CHI).
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Price to beat on a one-way flight from Vermont to Chicago (CHI).
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Find flight deals from Vermont to Chicago

Cheapest flights from Vermont to Chicago
Explore the most affordable flight options available from Vermont to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:40 amBTV - MDW
2 stops11h 57mDelta
Wed 9/34:25 pmMDW - BTV
1 stop5h 17mDelta
Deal found 7/2$210
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:30 pmBTV - ORD
1 stop5h 49mDelta
Wed 9/311:05 amORD - BTV
2 stops10h 37mDelta
Deal found 7/2$210
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/296:06 pmBDL - ORD
Nonstop2h 37mAmerican Airlines
Sat 8/28:41 pmORD - BDL
Nonstop2h 28mAmerican Airlines
Deal found 7/3$215
This Priceline deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1210:44 amBDL - ORD
1 stop7h 33mMultiple Airlines
Sat 7/195:01 amORD - BDL
1 stop5h 44mMultiple Airlines
Deal found 7/1$216
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/65:35 amBDL - MDW
1 stop4h 09mDelta
Wed 8/139:31 amMDW - BDL
1 stop5h 39mDelta
Deal found 6/30$217
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:00 amBDL - ORD
1 stop6h 46mUnited Airlines
Mon 9/84:00 pmORD - BDL
1 stop6h 44mUnited Airlines
Deal found 7/2$217
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/155:17 pmBDL - ORD
2 stops26h 50mSpirit Airlines
Sun 8/175:16 pmORD - BDL
2 stops15h 49mSpirit Airlines
Deal found 7/1$218
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:45 amBDL - MDW
2 stops8h 45mSouthwest
Sat 8/96:55 amMDW - BDL
1 stop6h 55mSouthwest
Deal found 7/1$219
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:04 pmBTV - ORD
Nonstop2h 40mAmerican Airlines
Sun 9/286:30 pmORD - BTV
Nonstop2h 25mAmerican Airlines
Deal found 7/3$219
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/244:47 pmBTV - ORD
Nonstop2h 37mUnited Airlines
Sun 7/276:35 pmORD - BTV
Nonstop2h 17mUnited Airlines
Deal found 7/1$226
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/159:52 amBDL - ORD
1 stop3h 58mDelta
Tue 7/227:10 amORD - BDL
1 stop3h 55mDelta
Deal found 7/1$227
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/289:15 amBDL - ORD
2 stops9h 40mSouthwest
Sun 8/313:00 pmORD - BDL
1 stop6h 20mSouthwest
Deal found 7/1$230

Cheapflights Fare Finder

Customize your flight search to find flights from Vermont to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
Use the filters below to find and compare flights from Vermont to Chicago that are best for you.

Fly from

Vermont

Fly to

Chicago

Route

Depart

Return

Price

BurlingtonChicago

BTV - MDW

BTVMDW

Burlington

Sat 8/30

6:40 am-5:37 pm

2 stops11h 57m

Chicago Midway

Wed 9/3

4:25 pm-10:42 pm

1 stop5h 17m

$210

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Sat 8/30

2:30 pm-7:19 pm

1 stop5h 49m

Chicago O'Hare Intl

Wed 9/3

11:05 am-10:42 pm

2 stops10h 37m

$210

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 7/27

7:00 am-8:38 am

Nonstop2h 38m

Chicago O'Hare Intl

Wed 7/30

2:06 pm-5:23 pm

Nonstop2h 17m

$215

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 8/6

5:35 am-8:44 am

1 stop4h 09m

Chicago Midway

Wed 8/13

9:31 am-4:10 pm

1 stop5h 39m

$217

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 8/15

5:17 pm-7:07 pm

2 stops26h 50m

Chicago O'Hare Intl

Sun 8/17

5:16 pm-10:05 am

2 stops15h 49m

$218

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 8/7

5:45 am-1:30 pm

2 stops8h 45m

Chicago Midway

Sat 8/9

6:55 am-2:50 pm

1 stop6h 55m

$219

BurlingtonChicago

BTV - ORD

BTVORD

Burlington

Mon 9/15

5:39 pm-7:18 pm

Nonstop2h 39m

Chicago O'Hare Intl

Mon 9/22

6:30 pm-9:55 pm

Nonstop2h 25m

$219

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 7/31

10:15 am-4:41 pm

1 stop7h 26m

Chicago O'Hare Intl

Sun 8/3

5:01 am-11:41 am

1 stop5h 40m

$220

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 8/14

6:00 am-7:48 am

Nonstop2h 48m

Chicago O'Hare Intl

Sat 8/16

6:15 pm-9:36 pm

Nonstop2h 21m

$223

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 8/30

1:20 pm-7:19 pm

1 stop6h 59m

Chicago O'Hare Intl

Tue 9/9

7:15 am-11:48 am

1 stop3h 33m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 55 results
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Best time to book a flight from Vermont to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Vermont with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Vermont to Chicago

What is the cheapest month to book a flight from Vermont to Chicago?

Currently, August is the cheapest month in which you can book a flight from Vermont to Chicago (average of $245). Flying from Vermont to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from VT to CHI?

Find hourly flight availability from Vermont to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

When flying from Vermont to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Vermont to Chicago

Explore weekly flight availability from Vermont to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 3, 2025.

The most flights from USVT to CHI are scheduled on a Thursday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Vermont to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Vermont to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Vermont to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Vermont to Chicago one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $79. Users have also found prices from $79 and $88 on United Airlines and Frontier, respectively.

  • What are the most popular routes from Vermont to Chicago?

    Most travelers choose Hartford Bradley Intl - Chicago O'Hare Intl, Albany Intl - Chicago O'Hare Intl or Hartford Bradley Intl - Chicago Midway when deciding on the best route from Vermont to Chicago.

  • What are the most reliable airlines from Vermont to Chicago?

    No one likes to see their flight delayed. When booking a flight from Vermont to Chicago consider choosing Republic Airways (98%), Qatar Airways (87%) or United Airlines (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Vermont to Chicago?

    Looking at all options, your cheapest flight can be booked for $194. While the most popular route (Hartford Bradley Intl - Chicago O'Hare Intl) can be booked for $132 on average our data indicates $978 when flying from Vermont to Chicago.

  • Can I find deals for flights from Vermont to Chicago that include hotel bookings?

    Yes. In addition to deals on Vermont to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Vermont to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vermont to Chicago.

  • Can I find deals for business class flights from Vermont to Chicago?

    Yes. Cheapflights offers flight deals from Vermont to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Vermont to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Vermont to Chicago (average of $245). Flying from Vermont to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Vermont?

Book flights to Vermont if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Vermont to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Vermont to Chicago

Discover the top 3 airlines that operate flights from Vermont to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$125Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$328FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$256Average$362FlexibilityNo cancel feeOn-time69%

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